This invention concerns alkyl esters of cyanoethoxyacetic acid and a process for preparing these compounds.
Acrylonitrile undergoes base-catalyzed addition reactions with practically any compound containing a reactive hydrogen, such as alcohols, mercaptans, hydrogen cyanide, acids, amines, phosphines and even ketones: EQU HZ + CH.sub.2 .dbd.CHCN .fwdarw. ZCH.sub.2 CH.sub.2 C.ident.N
sodium methoxide and sodium hydroxide have been used to catalyze the addition ofalcohols to acrylonitrile. Because the product contains a cyanoethyl group, the process has been called cyanoethylation.
However, the esters of hydroxy acids have resisted cyanoethylation. For instance, Organic Reactions, Vol. V, pg. 89 (1949) reports that attempts to add ethyl glycolate to acrylonitrile have failed, "... only the esters of hydroxy acids have resisted cyanoethylation; attempts to add ethyl glycolate, ethyl lactate, and ethyl ricinoleate to acrylonitrile have failed".